The expulsion of entire Jewish communities was among the most dramatic manifestations of increasing hostility toward Jews in late medieval Europe. Throughout this period, the Church remained formally committed to a doctrine of toleration developed by St. Augustine in the fourth century, a doctrine that looked to the Jew and ongoing Jewish exile as witness of Christian truth. Jewish expulsion was thus a theologically problematic proposition. This study turns to sermons, scholastic questions and treatises, legal decrees and chronicles to examine some of the ways Christian thinkers understood, justified, and criticized policies of expulsion, trying to reconcile Augustine’s doctrine of necessary tolerance with policies of absolute intolerance.